Highly diastereoselective reduction of chiral (ferrocenylseleno)methyl aryl and alkyl ketones

Chemistry Letters

Volumn , Issue 3, 1999, Pages 245-246

  Shirahata, Makoto ^a   Yamazaki, Hiroshi ^a   Fukuzawa, Shin Ichi ^a  

^a CHUO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033246936     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1999.245     Document Type: Article

References (27)

1. C. Paulmier, "Selenium Reagents and Intermediates in Organic Synthesis," Pergamon: Oxford (1986).
2. For a review, T. Wirth, Liebigs Ann./Recuil, 1997, 2189.
3. S. Fukuzawa, K. Takahashi, and H. Kato, J. Org. Chem., 62, 7711 (1997); S. Uemura, S. Fukuzawa, and Y. Nishibayashi, Chem. Comm., 1995, 2321.
4. S. Fukuzawa, K. Takahashi, and H. Kato, J. Org. Chem., 62, 7711 (1997); S. Uemura, S. Fukuzawa, and Y. Nishibayashi, Chem. Comm., 1995, 2321.
5. S. Uemura, S. Fukuzawa, and Y. Nishibayashi, J. Org. Chem., 60, 4114 (1995).
6. S. Uemura, S. Fukuzawa, and Y. Nishibayashi, Tetrahedron Lett., 35, 3115 (1994).
7. "Chirality in Industry," ed by A. N. Collins, G. N. Sheldrake, and J. Crosby; John Wiley: Chichester, (1994); "Chirality in Industry II," ed by A. N. Collins, G. N. Sheldrake, and J. Crosby; John Wiley: Chichester, (1997).
8. "Chirality in Industry," ed by A. N. Collins, G. N. Sheldrake, and J. Crosby; John Wiley: Chichester, (1994); "Chirality in Industry II," ed by A. N. Collins, G. N. Sheldrake, and J. Crosby; John Wiley: Chichester, (1997).
9. R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley: New York, (1994), Chap 2; H. Takaya, T. Ohta, and R. Noyori, "Asymmetric Hydrogenation," in "Catalytic Asymmetric Synthesis," ed by I. Ojima, VHC, Weinheim, (1993), pp 1-39.
10. R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley: New York, (1994), Chap 2; H. Takaya, T. Ohta, and R. Noyori, "Asymmetric Hydrogenation," in "Catalytic Asymmetric Synthesis," ed by I. Ojima, VHC, Weinheim, (1993), pp 1-39.
11. G. Solladie C. Frechou, Tetrahedron Lett., 25, 2867 (1986); H. Kosugi, H. Konta, and H. Uda, Chem. Comm., 1985, 211; G. Solladie, G. Demailly, J. Org. Chem., 50, 1552 (1985); G. Solladie and G. Demailly, Tetrahedron Lett., 26, 435 (1985); T. Nakata, T. Tanaka, and T. Oishi, Tetrahedron Lett., 26, 2653 (1983); A. Kover, T. Schottelius, and M. R. Hoffmann, Tetrahedron:Asymmetry, 2, 779 (1991).
12. G. Solladie C. Frechou, Tetrahedron Lett., 25, 2867 (1986); H. Kosugi, H. Konta, and H. Uda, Chem. Comm., 1985, 211; G. Solladie, G. Demailly, J. Org. Chem., 50, 1552 (1985); G. Solladie and G. Demailly, Tetrahedron Lett., 26, 435 (1985); T. Nakata, T. Tanaka, and T. Oishi, Tetrahedron Lett., 26, 2653 (1983); A. Kover, T. Schottelius, and M. R. Hoffmann, Tetrahedron:Asymmetry, 2, 779 (1991).
13. G. Solladie C. Frechou, Tetrahedron Lett., 25, 2867 (1986); H. Kosugi, H. Konta, and H. Uda, Chem. Comm., 1985, 211; G. Solladie, G. Demailly, J. Org. Chem., 50, 1552 (1985); G. Solladie and G. Demailly, Tetrahedron Lett., 26, 435 (1985); T. Nakata, T. Tanaka, and T. Oishi, Tetrahedron Lett., 26, 2653 (1983); A. Kover, T. Schottelius, and M. R. Hoffmann, Tetrahedron:Asymmetry, 2, 779 (1991).
14. G. Solladie C. Frechou, Tetrahedron Lett., 25, 2867 (1986); H. Kosugi, H. Konta, and H. Uda, Chem. Comm., 1985, 211; G. Solladie, G. Demailly, J. Org. Chem., 50, 1552 (1985); G. Solladie and G. Demailly, Tetrahedron Lett., 26, 435 (1985); T. Nakata, T. Tanaka, and T. Oishi, Tetrahedron Lett., 26, 2653 (1983); A. Kover, T. Schottelius, and M. R. Hoffmann, Tetrahedron:Asymmetry, 2, 779 (1991).
15. G. Solladie C. Frechou, Tetrahedron Lett., 25, 2867 (1986); H. Kosugi, H. Konta, and H. Uda, Chem. Comm., 1985, 211; G. Solladie, G. Demailly, J. Org. Chem., 50, 1552 (1985); G. Solladie and G. Demailly, Tetrahedron Lett., 26, 435 (1985); T. Nakata, T. Tanaka, and T. Oishi, Tetrahedron Lett., 26, 2653 (1983); A. Kover, T. Schottelius, and M. R. Hoffmann, Tetrahedron:Asymmetry, 2, 779 (1991).
16. G. Solladie C. Frechou, Tetrahedron Lett., 25, 2867 (1986); H. Kosugi, H. Konta, and H. Uda, Chem. Comm., 1985, 211; G. Solladie, G. Demailly, J. Org. Chem., 50, 1552 (1985); G. Solladie and G. Demailly, Tetrahedron Lett., 26, 435 (1985); T. Nakata, T. Tanaka, and T. Oishi, Tetrahedron Lett., 26, 2653 (1983); A. Kover, T. Schottelius, and M. R. Hoffmann, Tetrahedron:Asymmetry, 2, 779 (1991).
17. I. Ryu, S. Murai, I. Niwa, and N. Sonoda, Synthesis, 1977, 874; S. Murai, Y. Kuroki, K. Hasegawa, and S. Tsutsumi, Chem. Comm., 1972, 946.
18. I. Ryu, S. Murai, I. Niwa, and N. Sonoda, Synthesis, 1977, 874; S. Murai, Y. Kuroki, K. Hasegawa, and S. Tsutsumi, Chem. Comm., 1972, 946.
19. The stereochemisry of the alcoholic carbon in 4a (R= Ph) was independent from the reducing agents, being S configuration.
20. A. L. Gemal and J. L. Luche, J. Am. Chem. Soc., 103, 5454 (1981); J. Am. Chem. Soc., 100, 2226 (1978).
21. A. L. Gemal and J. L. Luche, J. Am. Chem. Soc., 103, 5454 (1981); J. Am. Chem. Soc., 100, 2226 (1978).
22. W. Dumont and A. Krief, Angew. Chem., 87, 347 (1975); J. L. Labourer, W. Dumont, and A. Krief, Tetrahedron Lett., 25, 4569 (1984).; S. Uemura, K. Ohe, and K. Sugita, Chem. Comm., 1988, 111.; W. H. Pirkle and P. L. Rinaldi, J. Org. Chem., 43, 3803 (1978).
23. W. Dumont and A. Krief, Angew. Chem., 87, 347 (1975); J. L. Labourer, W. Dumont, and A. Krief, Tetrahedron Lett., 25, 4569 (1984).; S. Uemura, K. Ohe, and K. Sugita, Chem. Comm., 1988, 111.; W. H. Pirkle and P. L. Rinaldi, J. Org. Chem., 43, 3803 (1978).
24. W. Dumont and A. Krief, Angew. Chem., 87, 347 (1975); J. L. Labourer, W. Dumont, and A. Krief, Tetrahedron Lett., 25, 4569 (1984).; S. Uemura, K. Ohe, and K. Sugita, Chem. Comm., 1988, 111.; W. H. Pirkle and P. L. Rinaldi, J. Org. Chem., 43, 3803 (1978).
25. W. Dumont and A. Krief, Angew. Chem., 87, 347 (1975); J. L. Labourer, W. Dumont, and A. Krief, Tetrahedron Lett., 25, 4569 (1984).; S. Uemura, K. Ohe, and K. Sugita, Chem. Comm., 1988, 111.; W. H. Pirkle and P. L. Rinaldi, J. Org. Chem., 43, 3803 (1978).
26. Reductive cleavage of C-Se bond by tin hydride in 4a (Fc*= Fa*, R= Ph) and 4c (Fc*= Fp*, R= Ph) afforded (R)-1-phenylethanol.
27. O. L. J. Cline, G. Chittatt, V, Faria, W. A. Kiel, S. M. Menchem, L. G. Singh, C. K. Wong, and N. J. Curtis, J. Am. Chem. Soc., 102, 4438 (1980).